Search Villas in Fleming Key

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Fleming Key Villas

Two Bedroom Two Bath Balcony Villa Steps from Duval!
Pool
Two Bedroom Two Bath Balcony Villa Steps from Duval!
10.0 out of 10, Exceptional, 35 reviews
"This place was perfect for a group of friends or family. The owners are so sweet and welcoming, and the property is clean and a great location. We will definitely be back."
The price is £457
per night
24 Jun - 25 Jun
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Pilar's Cottage by Brightwild | Studio w/Pool!
Pool
Pilar's Cottage by Brightwild | Studio w/Pool!
9.4 out of 10, Exceptional, 9 reviews
"Location could not be more ideal, walking to everything. Our host Jason was so accommodating and quick to respond to any needs we had."
The price is £278
per night
17 Jun - 18 Jun
Pilar's Cottage by Brightwild | Studio w/Pool!
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Pool | Outdoor pool
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
9.8 out of 10, Exceptional, 147 reviews
"We couldn’t have been happier with our choice to stay in this first class condo. It’s perfect. The condo itself is beautiful- along with amazing artwork that my wife didn’t stop talking about. The many outside spaces and pool are just perfect. And the location can’t be beat. We were a bit worried about the noise before we arrived because of the busy location - but it didn’t bother us at all. So if that’s a concern I wouldn’t worry about it. Just a perfect place to stay in Key West and would be...
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Pool
Two Bedroom Two Bath Poolside Villa Steps from Duval!
10.0 out of 10, Exceptional, 32 reviews
"I would not consider staying anywhere other than Key West Villas when visiting Key West. Hosts Kevin and his wife were super attentive, friendly and couldn't have been more hospitable! Our villa was well equipped and clean. Really enjoyed the daily Happy Hour gathering which included a wide variety of drinks and of course, the shot of the day! Look forward to returning here for another vacation!"
The price is £459
per night
19 Jun - 20 Jun
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Harborwalk Hideaways by Brightwild |Prime Location
Terrace/patio
Harborwalk Hideaways by Brightwild |Prime Location
10.0 out of 10, Exceptional, 3 reviews
"This property worked out fantastic for us. We had a large group for a bachelorette. We occupied the whole compound utilizing all 3 villas. The court yard with small pool was so cute and we loved sitting there and chatting about our previous night as a group while sipping our morning coffee. The rooms were super cute, clean and fit us all comfortably (we had 12 girls). We needed to contact the property managers a couple of times and they answered quickly and serviced our requests in a very timely...
The price is £1,887
per night
14 Jul - 15 Jul
Harborwalk Hideaways by Brightwild |Prime Location
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
Interior
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
4.0 star property
10.0 out of 10, Exceptional, 1 review
"The accommodations were very nice and comfortable. The place was clean and well maintained. TV/cable instructions would have been very helpful. The upstairs hallway smoke detector triggered for no apparent reason and i had to stand on a stool to deactivate it -kind of dangerous."
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Pool | Outdoor pool, a heated pool
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
9.8 out of 10, Exceptional, 70 reviews
"This property is ideal for a large group with plenty of space to spread out and also to gather. Perfectly located within walking distance of everything. Both units are very well appointed, extremely clean, and very comfortable. This is our second time renting this property, and we hope to do it again! We were better acclimated this time and enjoyed our stay that much more. So convenient and easy, and the property manager is super friendly and responsive."
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool
Beach nearby
Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool
9.6 out of 10, Exceptional, 5 reviews
"Nice place"
Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool
Poolside Studio Villa Steps from Duval!
Pool
Poolside Studio Villa Steps from Duval!
10.0 out of 10, Exceptional, 12 reviews
"Great communication from the time of booking. Great people to deal with and excellent location. Quiet area. Love the happy hour they offer too!"
Poolside Studio Villa Steps from Duval!
Coral Palm by AvantStay | Key West Walkable
Outdoor dining
Coral Palm by AvantStay | Key West Walkable
9.6 out of 10, Exceptional, 9 reviews
"Property was very nice and clean in a gated community. After we arrived we went to fix supper and discovered the oven was NOT working. With it being around the holidays they were not able to get a repairman to get it fixed until after our stay. I would have appreciated some type of little refund as the reason we like VRBO’s is so we can eat one meal a day a home and not have to eat out all the time. 7 people eating out all the time gets expensive in a hurry. And we had already grabbed a few...
Coral Palm by AvantStay | Key West Walkable
Coral Villa by AvantStay | Close 2 DT Key West
Property grounds
Coral Villa by AvantStay | Close 2 DT Key West
9.2 out of 10, Wonderful, 27 reviews
"Great location and great access. Safe and secure."
Coral Villa by AvantStay | Close 2 DT Key West
African Queen by Brightwild | GREAT Suite
1 bedroom, desk, iron/ironing board, WiFi
African Queen by Brightwild | GREAT Suite
7.6 out of 10, Good, 5 reviews
"Location of property offers convenient access to historic downtown whenever you want. However, the option to privately and quietly spend time in the outside area is there as well. Well maintained property,"
The price is £418
per night
30 Jun - 1 Jul
African Queen by Brightwild | GREAT Suite
Loft Villa Steps from Duval!
Pool
Loft Villa Steps from Duval!
10.0 out of 10, Exceptional, 7 reviews
"The location was perfect and the owners were amazing. The breakfast and happy hour were wonderful, I was always receiving texts to check on us. Would definitely stay here again!"
Loft Villa Steps from Duval!
The Villa of Pelico Palms
Beach
The Villa of Pelico Palms
10.0 out of 10, Exceptional, 1 review
"Great location and nice homeowners. We would stay again."
The Villa of Pelico Palms
Poolside Queen Room Steps from Duval!
Pool
Poolside Queen Room Steps from Duval!
10.0 out of 10, Exceptional, 1 review
"Perfect location, awesome hosts, and the Key West Villas were wonderful. The pool area provided a tranquil area to relax."
Poolside Queen Room Steps from Duval!
One Bedroom Deck Villa Steps from Duval!
Pool
One Bedroom Deck Villa Steps from Duval!
10.0 out of 10, Exceptional, 6 reviews
"Outstanding place to stay! Awesome amenities and great location! A definite stay and a place to return again! Nice continental breakfast, afternoon snacks, excellent happy hour and specialty shot of the day! Beautiful grounds, great pool, awesome hosts too! Thanks for a great stay at Key West Villas!"
One Bedroom Deck Villa Steps from Duval!
Poolside King Room Steps from Duval!
Pool
Poolside King Room Steps from Duval!
10.0 out of 10, Exceptional, 1 review
"If you’re looking to stay in Old Town this is the perfect location. Pool right outside the room, FREE Happy Hour from 4-5 and very accommodating hosts. Good for families or couples alike. Awesome!"
The price is £355
per night
29 Jun - 30 Jun
Poolside King Room Steps from Duval!
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
Pool
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
10.0 out of 10, Exceptional, 4 reviews
"Our 2nd trip to Hyatt Beach Resort and love everything about it! Bathrooms were recently updated and place was clean, staff helpful and we'd go back again!"
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
Duval Penthouse
Lobby sitting area
Duval Penthouse
4.0 star property
Duval Penthouse
Don't see what you're looking for?
See all available properties in Fleming Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Fleming Key

Steps from Duval, Pool & Bikes $129-$299 Night!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, 334 reviews
"Listing was accurate. Scuba masks were available and beach chairs which was a great surprise. Room was very clean. Great location and great communication. We will definitely stay again. Thank you!"
The price is £191
per night
20 Jun - 21 Jun
Steps from Duval, Pool & Bikes $129-$299 Night!
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, 100 reviews
"Nice spot away from the crowd but close enough to walk/scoot/bike to. If you plan on parking its first come first serve and not a lot of room for vehicles in the gravel driveway. Maybe 5 cars max if guests know how to park efficiently. If not then youll have to scout the street for a spare spot. I rented a scooter so no issue for finding parking in the driveway. Easy check in and the room( I stayed in the Havana) was small but big enough for one person; two if your spouse packs light and is easy...
The price is £220
per night
17 Jun - 18 Jun
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Aqua Lodges at Hurricane Hole Marina
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, 91 reviews
"We received info on how to check in via self-service. Very easy to check in and get our key to the lodge. Lodge itself was clean and adorable. We loved sitting on the deck watching the water and the floating tikis. Would go back for sure"
The price is £221
per night
21 Jun - 22 Jun
Aqua Lodges at Hurricane Hole Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fleming Key Villas information

Number of reviews
Accommodation
 Villas
Lowest Price
Highest Price

Frequently asked questions

Why book your holiday villa in Fleming Key with Expedia?
We think arranging a holiday shouldn’t be hard, so if you’re in search of villas at a competitive rate, Expedia has you covered. Save those pennies and select an all-inclusive stay, or splurge on a luxe holiday villa to surprise your loved ones. Our search filters make it simple to find a retreat in Fleming Key that you’ll adore.
How can I find cheap villas in Fleming Key?
With Expedia’s handy filter tool, sourcing cheap villas in Fleming Key is a cinch. To find stays that give you the most bang for your buck, refine your search results by budget, amenities and star rating.

Fleming Key Hotel Reviews
Expedia verified reviews

Margaritaville Beach House Key West

Margaritaville Beach House Key West

5/5 Excellent
"Was a very nice place to stay. Food at the restaurant is limited on options but it is good. Drink prices are the same as in town. The staff was super welcoming and nice throughout our stay. They helped and asked if you needed anything constantly. The airport transportation was on time and friendly. The downtown transportation was ok the two ladies were not very personable, Vee didn't say anything to anyone. Not even watch your step have a nice time hope you get hit by a bus nothing. The gentleman he was the nicest and gave the most information about the town. Luanne did say when the bus left and some facts the first time we rode it with her, she may of just been having a bad day or recognized everyone the other time we rode with her."
A verified traveller from Maineville stayed at Margaritaville Beach House Key West
Posted 2 days ago
Margaritaville Beach House Key West